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US 5,290,948 AGranted
Process for producing polyhydroxylated piperidines and pyrrolidines and compounds thereof
AssigneeMcNeilab, Inc.
InventorsAllen B. Reitz, Ellen W. Baxter, Bruce E. Maryanoff
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Abstract
A process for converting 1,4- and 1,5-dicarbonyl sugars to pyrrolidine and piperidine amino sugars. Novel compounds resulting from this process are also described.
Claims13
A method for the synthesis of a compound of the formula I and stereoisomers thereof;
- ##STR13## wherein n=1 and R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of CH.sub.2 OH, CH.sub.3 H, and CH.sub.2 F;
- wherein R.sup.3 is selected from the group consisting of H, straight and branched C.sub.1 -C.sub.20 alkyl, substituted straight and branched C.sub.1 -C.sub.20 alkyl, aralkyl, phenyl, substituted phenyl, heteroaryl, alkyl amino, aryl amino, amino, alkyl oxy and aralkyl oxy, with the proviso that R.sup.3 cannot be a group such that a carbon atom attached to the ring nitrogen is a quaternary carbon atom, which comprises reacting a compound of the formula II:
- ##STR14## wherein n=1 or 2;
- with an amine of the formula R.sup.3 NH.sub.2 ;
- said reaction being carried out in the presence of an acid and a source of hydride.
2 more elements
Dependencies are inferred from the claim text.